Sodium Hydroxide → (R)-2-(4-chloro-3-fluorophenyl)oxirane

HRID 530588ノート

反応式

HRID 530588 の反応式
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([F:22])[CH:16]=2)[OH:14])(=O)=O)=CC=1.FC1C=CC(C(=O)C)=CC=1C(F)(F)F.[OH-].[Na+]>CCOCC>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@H:13]2[CH2:12][O:14]2)=[CH:16][C:17]=1[F:22]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 117870261(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

生成物 1

HCID 94590788(R)-2-(4-chloro-3-fluorophenyl)oxirane

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (prepared as previously described in Example 1 (steps a-b) except substituting 1-(3-chloro-4-fluorophenyl)ethanone for 1-(4-fluoro-3-(trifluoromethyl)phenyl)ethanone, 3.35 g, 9.72 mmol) was dissolved in ether (80 mL) and 2N NaOH solution (25 mL) was added. The mixture was stirred at room temperature for 6 h until all starting material was consumed. The mixture was separated and the ether layer was washed with water. The organic layer was dried with sodium sulfate and solvents were removed to afford (R)-2-(4-chloro-3-fluorophenyl)oxirane as a colorless oil which was dried in vacuum (1.66 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.71-2.80 (m, 1H) 3.18 (dd, J=5.31, 4.04 Hz, 1H) 3.82-3.89 (m, 1H) 7.01-7.12 (m, 2H) 7.39 (dd, J=8.46, 7.45 Hz, 1H).

後処理

  1. customwas consumed
  2. customThe mixture was separated
  3. washthe ether layer was washed with water
  4. dry with materialThe organic layer was dried with sodium sulfate and solvents
  5. customwere removed

出典と根拠

ORDレコード
ord-226c60bdf29f44469e0c0d048a6b01b2
出典データセット
uspto-grants-2016_05
特許番号
US09353096B2

反応ノート

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